SA519401049B1 - مشتقات ثيوفين مكثفة مفيدة كمثبطات ناقل مشترك فوسفات يعتمد على أيون الصوديوم iiب - Google Patents
مشتقات ثيوفين مكثفة مفيدة كمثبطات ناقل مشترك فوسفات يعتمد على أيون الصوديوم iiب Download PDFInfo
- Publication number
- SA519401049B1 SA519401049B1 SA519401049A SA519401049A SA519401049B1 SA 519401049 B1 SA519401049 B1 SA 519401049B1 SA 519401049 A SA519401049 A SA 519401049A SA 519401049 A SA519401049 A SA 519401049A SA 519401049 B1 SA519401049 B1 SA 519401049B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- amino
- methyl
- phenyl
- difluoro
- ethyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title description 5
- 150000003577 thiophenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 150
- 239000000203 mixture Substances 0.000 abstract description 111
- 150000003839 salts Chemical class 0.000 abstract description 61
- 201000005991 hyperphosphatemia Diseases 0.000 abstract description 32
- 208000020832 chronic kidney disease Diseases 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 370
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 291
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 223
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 201
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 186
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 137
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 133
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 127
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 113
- 239000000243 solution Substances 0.000 description 88
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 83
- 239000007787 solid Substances 0.000 description 78
- 239000000047 product Substances 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 239000002253 acid Substances 0.000 description 64
- -1 piperazine-1-yl Chemical group 0.000 description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
- 229910019142 PO4 Inorganic materials 0.000 description 54
- 239000010452 phosphate Substances 0.000 description 54
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 52
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 51
- 239000011541 reaction mixture Substances 0.000 description 47
- 238000011282 treatment Methods 0.000 description 47
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 45
- 230000002829 reductive effect Effects 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 44
- 239000002904 solvent Substances 0.000 description 44
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 41
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 40
- 235000019253 formic acid Nutrition 0.000 description 40
- 239000010410 layer Substances 0.000 description 38
- 239000012044 organic layer Substances 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 35
- 239000011734 sodium Substances 0.000 description 35
- 238000005481 NMR spectroscopy Methods 0.000 description 33
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- 239000000725 suspension Substances 0.000 description 31
- 238000004587 chromatography analysis Methods 0.000 description 30
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
- 238000001704 evaporation Methods 0.000 description 27
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- 230000001419 dependent effect Effects 0.000 description 26
- 230000008020 evaporation Effects 0.000 description 26
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 26
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- 230000001684 chronic effect Effects 0.000 description 18
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- 229920006395 saturated elastomer Polymers 0.000 description 18
- 238000012360 testing method Methods 0.000 description 17
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- 230000005764 inhibitory process Effects 0.000 description 16
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
- 150000001350 alkyl halides Chemical class 0.000 description 13
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
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- 210000000941 bile Anatomy 0.000 description 11
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- 239000007858 starting material Substances 0.000 description 7
- 229940126657 Compound 17 Drugs 0.000 description 6
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- 239000000872 buffer Substances 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 5
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- DAKIDYQCFJQMDF-UHFFFAOYSA-N dichloromethane;pyridine Chemical compound ClCCl.C1=CC=NC=C1 DAKIDYQCFJQMDF-UHFFFAOYSA-N 0.000 description 1
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- 238000003209 gene knockout Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- NZPIUJUFIFZSPW-UHFFFAOYSA-H lanthanum carbonate Chemical compound [La+3].[La+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O NZPIUJUFIFZSPW-UHFFFAOYSA-H 0.000 description 1
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- CAABRJFUDNBRJZ-UHFFFAOYSA-N methyl 4-ethylbenzoate Chemical compound CCC1=CC=C(C(=O)OC)C=C1 CAABRJFUDNBRJZ-UHFFFAOYSA-N 0.000 description 1
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- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- XNQULTQRGBXLIA-UHFFFAOYSA-O phosphonic anhydride Chemical compound O[P+](O)=O XNQULTQRGBXLIA-UHFFFAOYSA-O 0.000 description 1
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- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
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- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229960005441 sevelamer carbonate Drugs 0.000 description 1
- 229960003027 sevelamer hydrochloride Drugs 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 108091006284 sodium-phosphate co-transporters Proteins 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
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- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- WZKATXIWWWRHEB-UHFFFAOYSA-N tert-butyl 4-(4-hydroxybutylcarbamoyl)-2,2-dimethylpiperazine-1-carboxylate Chemical compound OCCCCNC(=O)N1CC(N(CC1)C(=O)OC(C)(C)C)(C)C WZKATXIWWWRHEB-UHFFFAOYSA-N 0.000 description 1
- FAJLDEROPURCJQ-UHFFFAOYSA-N tert-butyl 4-[(3-methoxy-3-oxopropyl)carbamoyl]-2,2-dimethylpiperazine-1-carboxylate Chemical compound COC(CCNC(=O)N1CC(N(CC1)C(=O)OC(C)(C)C)(C)C)=O FAJLDEROPURCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4995—Pyrazines or piperazines forming part of bridged ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Inorganic Chemistry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662375169P | 2016-08-15 | 2016-08-15 | |
| PCT/US2017/045843 WO2018034883A1 (fr) | 2016-08-15 | 2017-08-08 | Dérivés de thiophène condensés utiles en tant qu'inhibiteurs de napi-iib |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SA519401049B1 true SA519401049B1 (ar) | 2021-07-14 |
Family
ID=59677343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SA519401049A SA519401049B1 (ar) | 2016-08-15 | 2019-02-07 | مشتقات ثيوفين مكثفة مفيدة كمثبطات ناقل مشترك فوسفات يعتمد على أيون الصوديوم iiب |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US10934280B2 (fr) |
| EP (1) | EP3497091B1 (fr) |
| JP (1) | JP6653410B2 (fr) |
| KR (1) | KR102266143B1 (fr) |
| CN (1) | CN109563070B (fr) |
| AU (1) | AU2017312783B2 (fr) |
| BR (1) | BR112019000929A2 (fr) |
| CA (1) | CA3033628C (fr) |
| CY (1) | CY1123576T1 (fr) |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11202105190SA (en) * | 2018-11-19 | 2021-06-29 | 11949098 Canada Inc | 4,5,6,7-tetrahydro-l-benzothiophene modulators of retinoic acid receptor related (rar) orphan nuclear receptors (rors) |
| CN113784956A (zh) * | 2019-05-16 | 2021-12-10 | 伊莱利利公司 | 钠-氢交换体3抑制剂化合物 |
| MX2023014507A (es) | 2021-06-08 | 2024-01-26 | Chugai Pharmaceutical Co Ltd | Formulacion que contiene un derivado de dihidropiridazina-3,5-dion a. |
| AR126060A1 (es) | 2021-06-08 | 2023-09-06 | Chugai Pharmaceutical Co Ltd | Método para producir derivado de dihidropiridazin-3,5-diona |
| WO2023219127A1 (fr) * | 2022-05-11 | 2023-11-16 | 中外製薬株式会社 | Composition pharmaceutique pour le traitement ou la prévention d'une maladie kystique |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2539722T3 (es) * | 2010-04-28 | 2015-07-03 | Astellas Pharma Inc. | Compuesto de tetrahidrobenzotiofeno |
| MX342521B (es) * | 2011-10-27 | 2016-10-03 | Astellas Pharma Inc | Derivado de n-tienilbenzamida sustituido con aminoalquilo. |
| WO2014003153A1 (fr) * | 2012-06-28 | 2014-01-03 | 協和発酵キリン株式会社 | Composé amide substitué |
| CN105658635B (zh) | 2014-08-22 | 2019-03-08 | 江苏恒瑞医药股份有限公司 | 噻吩并环烷基或噻吩并杂环基类衍生物、其制备方法及其在医药上的应用 |
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| AU2017312783A1 (en) | 2019-01-24 |
| MX2019001781A (es) | 2019-07-04 |
| HUE052351T2 (hu) | 2021-04-28 |
| WO2018034883A1 (fr) | 2018-02-22 |
| US10934280B2 (en) | 2021-03-02 |
| ES2830444T3 (es) | 2021-06-03 |
| NZ750153A (en) | 2021-01-29 |
| AU2017312783B2 (en) | 2020-02-06 |
| PT3497091T (pt) | 2020-11-30 |
| EA037376B1 (ru) | 2021-03-22 |
| EP3497091B1 (fr) | 2020-10-07 |
| IL264785B (en) | 2021-04-29 |
| RS61165B1 (sr) | 2021-01-29 |
| KR20190026895A (ko) | 2019-03-13 |
| SI3497091T1 (sl) | 2020-11-30 |
| KR102266143B1 (ko) | 2021-06-17 |
| LT3497091T (lt) | 2020-12-28 |
| BR112019000929A2 (pt) | 2019-07-09 |
| JP6653410B2 (ja) | 2020-02-26 |
| ZA201900305B (en) | 2020-12-23 |
| EA201990095A1 (ru) | 2019-07-31 |
| HRP20202025T1 (hr) | 2021-02-19 |
| JP2019527734A (ja) | 2019-10-03 |
| US20200031813A1 (en) | 2020-01-30 |
| PL3497091T3 (pl) | 2021-02-08 |
| EP3497091A1 (fr) | 2019-06-19 |
| CA3033628A1 (fr) | 2018-02-22 |
| CA3033628C (fr) | 2021-01-12 |
| CN109563070B (zh) | 2021-02-26 |
| DK3497091T3 (da) | 2020-10-19 |
| CN109563070A (zh) | 2019-04-02 |
| CY1123576T1 (el) | 2022-03-24 |
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